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Find cheap flights from Chicago Midway Airport to Jamaica from $99

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Jamaica departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Tue 6/4
Tue 6/11

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Best Jamaica Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Montego Bay
Montego Bay1 stop$320
Kingston
Kingston1 stop$480

Good to know

Low season

July

High season

October

Cheapest flight

$99
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Chicago Midway Airport to Montego Bay

FAQs - booking Jamaica flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Jamaica?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Jamaica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Jamaica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Jamaica from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Jamaica?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Jamaica with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Jamaica?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Jamaica from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Jamaica

  • Morning departure is around 12% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top airlines flying from Midway to Jamaica

 
Need help choosing which airline to fly with from Midway to Jamaica? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10826 reviews
7.9Comfort
7.4Food
8.6Crew
8.0Entertainment
8.2Boarding
Airline reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

8.0 ExcellentCynthia, May 2024ATL - TYS
Read more about Delta reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Chicago to Jamaica

Recent round-trip flight deals

9/5Thu
1 stopFrontier
9h 13mMDW-MBJ
9/10Tue
1 stopFrontier
12h 42mMBJ-MDW
$320
8/6Tue
1 stopFrontier
17h 02mMDW-MBJ
8/13Tue
1 stopFrontier
13h 03mMBJ-MDW
$327
8/7Wed
1 stopFrontier
7h 19mMDW-MBJ
8/13Tue
1 stopFrontier
13h 03mMBJ-MDW
$328
5/18Sat
1 stopFrontier
7h 42mMDW-MBJ
5/25Sat
1 stopFrontier
13h 29mMBJ-MDW
$346
8/2Fri
1 stopFrontier
23h 30mMDW-MBJ
8/6Tue
1 stopFrontier
13h 03mMBJ-MDW
$358
5/26Sun
1 stop
20h 41mMDW-MBJ
6/1Sat
2 stops
28h 27mMBJ-MDW
$361
6/1Sat
1 stop
7h 42mMDW-MBJ
6/8Sat
2 stops
9h 01mMBJ-MDW
$405
10/20Sun
1 stopDelta
5h 36mMDW-MBJ
10/25Fri
1 stopDelta
16h 52mMBJ-MDW
$468
9/18Wed
1 stopDelta
6h 42mMDW-KIN
9/26Thu
1 stopDelta
12h 44mKIN-MDW
$480
5/17Fri
2 stopsWestJet
21h 29mMDW-KIN
5/24Fri
2 stopsWestJet
20h 57mKIN-MDW
$3,110

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Recent one-way flight deals

5/14Tue
1 stopFrontier
7h 53mMDW-MBJ
$99
5/18Sat
1 stopFrontier
24h 18mMDW-MBJ
$135
5/18Sat
2 stops
14h 33mMDW-MBJ
$171
6/2Sun
1 stopFrontier
11h 02mMDW-MBJ
$182
5/20Mon
1 stopFrontier
23h 04mMDW-MBJ
$204
5/20Mon
2 stops
20h 05mMDW-MBJ
$218
9/25Wed
1 stopFrontier
9h 13mMDW-MBJ
$227
6/6Thu
2 stopsDelta
10h 24mMDW-KIN
$267
9/26Thu
2 stopsDelta
17h 23mMDW-MBJ
$389
5/14Tue
2 stopsWestJet
19h 06mMDW-MBJ
$1,913

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Last minute flights from Midway to Jamaica

Last minute flight, train and bus deals

5/7Tue
multi-stopFrontier
11h 04mMDW-MBJ
5/14Tue
multi-stopFrontier
10h 43mMBJ-MDW
$285
5/8Wed
multi-stopFrontier
24h 20mMDW-MBJ
5/11Sat
multi-stopFrontier
10h 50mMBJ-MDW
$357
5/10Fri
multi-stopFrontier
16h 30mMDW-MBJ
5/14Tue
multi-stopFrontier
10h 43mMBJ-MDW
$410
5/8Wed
multi-stopFrontier
24h 20mMDW-MBJ
5/10Fri
multi-stopFrontier
35h 47mMBJ-MDW
$414
5/7Tue
multi-stopDelta
9h 34mMDW-MBJ
5/8Wed
multi-stopDelta
14h 56mMBJ-MDW
$548
5/7Tue
multi-stopDelta
5h 39mMDW-MBJ
5/8Wed
multi-stopDelta
14h 56mMBJ-MDW
$669
5/9Thu
multi-stop
18h 04mMDW-MBJ
5/12Sun
multi-stop
23h 30mMBJ-MDW
$677
5/8Wed
multi-stop
28h 25mMDW-KIN
5/10Fri
multi-stop
24h 02mKIN-MDW
$869
5/10Fri
multi-stopWestJet
12h 26mMDW-MBJ
5/14Tue
multi-stopWestJet
26h 55mMBJ-MDW
$3,675
5/8Wed
multi-stopWestJet
23h 05mMDW-MBJ
5/11Sat
multi-stopWestJet
19h 45mMBJ-MDW
$3,916

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Chicago Midway Airport - Jamaica Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Jamaica - Chicago Midway Airport

Cabin classes: